US7714131B2 - Process for the stereoselective preparation of (−)-halofenate and derivatives thereof - Google Patents
Process for the stereoselective preparation of (−)-halofenate and derivatives thereof Download PDFInfo
- Publication number
- US7714131B2 US7714131B2 US11/525,200 US52520006A US7714131B2 US 7714131 B2 US7714131 B2 US 7714131B2 US 52520006 A US52520006 A US 52520006A US 7714131 B2 US7714131 B2 US 7714131B2
- Authority
- US
- United States
- Prior art keywords
- formula
- group
- compound
- subscript
- compatible solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
Links
- 0 [1*]C(=O)C(OC1=CC(C(F)(F)F)=CC=C1)C1=CC=C(Cl)C=C1 Chemical compound [1*]C(=O)C(OC1=CC(C(F)(F)F)=CC=C1)C1=CC=C(Cl)C=C1 0.000 description 26
- REBNNLOCRFCEPD-UHFFFAOYSA-N CC(C)OC(C(=O)N1CCCC1)C(OC(C)C)C(=O)N1CCCC1.CC(C)OC(C)C(=O)N1CCCC1.CC(C)OC(C)C(=O)N1CCN(C(=O)C(C)OC(C)C)CC1.CC(C)OC(C)C(=O)N1CCOCC1 Chemical compound CC(C)OC(C(=O)N1CCCC1)C(OC(C)C)C(=O)N1CCCC1.CC(C)OC(C)C(=O)N1CCCC1.CC(C)OC(C)C(=O)N1CCN(C(=O)C(C)OC(C)C)CC1.CC(C)OC(C)C(=O)N1CCOCC1 REBNNLOCRFCEPD-UHFFFAOYSA-N 0.000 description 2
- KDCMNKPQYHXION-LFFJXTNRSA-N CC(OC(=O)[C@H](OC1=CC(C(F)(F)F)=CC=C1)C1=CC=C(Cl)C=C1)C(=O)N1CCCC1.CC(OC(=O)[C@H](OC1=CC(C(F)(F)F)=CC=C1)C1=CC=C(Cl)C=C1)C(=O)N1CCN(C(=O)[C@H](C)OC(=O)[C@H](OC2=CC(C(F)(F)F)=CC=C2)C2=CC=C(Cl)C=C2)CC1.CC(OC(=O)[C@H](OC1=CC(C(F)(F)F)=CC=C1)C1=CC=C(Cl)C=C1)C(=O)N1CCOCC1.O=C(OC(C(=O)N1CCCC1)[C@H](OC(=O)[C@H](OC1=CC=CC(C(F)(F)F)=C1)C1=CC=C(Cl)C=C1)C(=O)N1CCCC1)C(OC1=CC=CC(C(F)(F)F)=C1)C1=CC=C(Cl)C=C1 Chemical compound CC(OC(=O)[C@H](OC1=CC(C(F)(F)F)=CC=C1)C1=CC=C(Cl)C=C1)C(=O)N1CCCC1.CC(OC(=O)[C@H](OC1=CC(C(F)(F)F)=CC=C1)C1=CC=C(Cl)C=C1)C(=O)N1CCN(C(=O)[C@H](C)OC(=O)[C@H](OC2=CC(C(F)(F)F)=CC=C2)C2=CC=C(Cl)C=C2)CC1.CC(OC(=O)[C@H](OC1=CC(C(F)(F)F)=CC=C1)C1=CC=C(Cl)C=C1)C(=O)N1CCOCC1.O=C(OC(C(=O)N1CCCC1)[C@H](OC(=O)[C@H](OC1=CC=CC(C(F)(F)F)=C1)C1=CC=C(Cl)C=C1)C(=O)N1CCCC1)C(OC1=CC=CC(C(F)(F)F)=C1)C1=CC=C(Cl)C=C1 KDCMNKPQYHXION-LFFJXTNRSA-N 0.000 description 2
- KLCGBSXTJWOEJD-LURJTMIESA-N C[C@H](O)C(=O)N1CCCC1 Chemical compound C[C@H](O)C(=O)N1CCCC1 KLCGBSXTJWOEJD-LURJTMIESA-N 0.000 description 2
- XMQSCSACRZNLPC-UHFFFAOYSA-N CC(C)OC(C)C(=O)N1CCCC1 Chemical compound CC(C)OC(C)C(=O)N1CCCC1 XMQSCSACRZNLPC-UHFFFAOYSA-N 0.000 description 1
- RCEBQTGDEMAEMU-IEUDWUHUSA-N CC(O)C(=O)N1CCCC1.CC(OC(=O)C(Br)C1=CC=C(Cl)C=C1)C(=O)N1CCCC1.CC(OC(=O)C(OC1=CC(C(F)(F)F)=CC=C1)C1=CC=C(Cl)C=C1)C(=O)N1CCCC1.O=C(O)CC1=CC=C(Cl)C=C1.O=C(O)[C@H](OC1=CC=CC(C(F)(F)F)=C1)C1=CC=C(Cl)C=C1.OC1=CC(C(F)(F)F)=CC=C1 Chemical compound CC(O)C(=O)N1CCCC1.CC(OC(=O)C(Br)C1=CC=C(Cl)C=C1)C(=O)N1CCCC1.CC(OC(=O)C(OC1=CC(C(F)(F)F)=CC=C1)C1=CC=C(Cl)C=C1)C(=O)N1CCCC1.O=C(O)CC1=CC=C(Cl)C=C1.O=C(O)[C@H](OC1=CC=CC(C(F)(F)F)=C1)C1=CC=C(Cl)C=C1.OC1=CC(C(F)(F)F)=CC=C1 RCEBQTGDEMAEMU-IEUDWUHUSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N OC(Cc1ccccc1)=O Chemical compound OC(Cc1ccccc1)=O WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (18)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/525,200 US7714131B2 (en) | 2005-09-23 | 2006-09-20 | Process for the stereoselective preparation of (−)-halofenate and derivatives thereof |
DK06815150.5T DK1940387T3 (da) | 2005-09-23 | 2006-09-21 | Fremgangsmåde til stereoselektiv fremstilling af (-)-halofenat og mellemprodukter deraf |
EA200800884A EA015673B1 (ru) | 2005-09-23 | 2006-09-21 | Способ стереоселективного получения (-)-галофената и его интермедиатов |
PT68151505T PT1940387E (pt) | 2005-09-23 | 2006-09-21 | Processo para a preparação estereosselectiva de (-)-halofenato e seus intermediários |
KR1020087009709A KR101309605B1 (ko) | 2005-09-23 | 2006-09-21 | (―)―할로페네이트 및 이의 중간체의 입체 선택적제조를 위한 방법 |
JP2008532404A JP2009515817A (ja) | 2005-09-23 | 2006-09-21 | (−)−ハロフェナートおよびその中間体の立体選択的調製のための方法 |
ES06815150T ES2394973T3 (es) | 2005-09-23 | 2006-09-21 | Procedimiento para la preparación estereoselectiva de (-)-halofenato e intermedios para el mismo |
PL06815150T PL1940387T3 (pl) | 2005-09-23 | 2006-09-21 | Sposób stereoselektywnego wytwarzania (-)-halofenatu i jego półproduktów |
PCT/US2006/036928 WO2007038243A1 (en) | 2005-09-23 | 2006-09-21 | Process for the stereoselective preparation of (-)-halofenate and intermediates thereof |
RS20130001A RS52608B (en) | 2005-09-23 | 2006-09-21 | PROCEDURE FOR STEREOSELECTIVE PREPARATION (-) - HALOPHENATES AND ITS INTERMEDIATES |
AU2006294950A AU2006294950A1 (en) | 2005-09-23 | 2006-09-21 | Process for the stereoselective preparation of (-)-halofenate and intermediates thereof |
SI200631502T SI1940387T1 (sl) | 2005-09-23 | 2006-09-21 | Postopek za stereoselektivno pripravo (-) halofenata in njegovih intermediatov |
EP06815150A EP1940387B1 (en) | 2005-09-23 | 2006-09-21 | Process for the stereoselective preparation of (-)-halofenate and intermediates thereof |
CA2623350A CA2623350C (en) | 2005-09-23 | 2006-09-21 | Process for the stereoselective preparation of (-)-halofenate and intermediates thereof |
BRPI0616188-0A BRPI0616188A2 (pt) | 2005-09-23 | 2006-09-21 | mÉtodos para preparar um composto, e para preparar (-)-halofenato, composto, e, composiÇço |
IL190325A IL190325A (en) | 2005-09-23 | 2008-03-20 | A process for making loopfin |
HK08114045.8A HK1119953A1 (en) | 2005-09-23 | 2008-12-29 | Process for the stereoselective preparation of (-)-halofenate and intermediates thereof |
HRP20130001TT HRP20130001T1 (hr) | 2005-09-23 | 2013-01-02 | Postupak za stereoselektivno pripremanje (-)-halofenata i njegovih intermedijara |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US72030005P | 2005-09-23 | 2005-09-23 | |
US11/525,200 US7714131B2 (en) | 2005-09-23 | 2006-09-20 | Process for the stereoselective preparation of (−)-halofenate and derivatives thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
US20070072858A1 US20070072858A1 (en) | 2007-03-29 |
US7714131B2 true US7714131B2 (en) | 2010-05-11 |
Family
ID=37894903
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/525,200 Expired - Fee Related US7714131B2 (en) | 2005-09-23 | 2006-09-20 | Process for the stereoselective preparation of (−)-halofenate and derivatives thereof |
Country Status (18)
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100093854A1 (en) * | 2008-04-03 | 2010-04-15 | Diego Broggini | Process for the preparation of (-)-(4-chloro-phenyl)-(3-trifluoromethyl-phenoxy)-acetic acid 2-acetylamino-ethyl ester |
US9023856B2 (en) | 2011-11-04 | 2015-05-05 | Cymabay Therapeutics, Inc. | Methods for treating hyperuricemia in patients with gout using halofenate or halogenic acid and a second urate-lowering agent |
US9060987B2 (en) | 2011-11-04 | 2015-06-23 | Cymabay Therapeutics, Inc. | Methods for treating gout flares |
WO2021236395A1 (en) | 2020-05-18 | 2021-11-25 | Cymabay Therapeutics, Inc. | Cb-0406 choline salt |
WO2021236394A1 (en) | 2020-05-18 | 2021-11-25 | Cymabay Therapeutics, Inc. | Cb-0406 tromethamine salt |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2298729A4 (en) * | 2008-06-03 | 2012-12-19 | Kaneka Corp | PROCESS FOR PRODUCING OPTICALLY ACTIVE AMINO ACID DERIVATIVE |
Citations (69)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1476525A (fr) | 1964-03-20 | 1967-04-14 | Merck & Co Inc | Nouveaux acides alkanoïques à substituant aryle et procédés pour leur préparation |
US3444299A (en) | 1964-02-07 | 1969-05-13 | American Cyanamid Co | Methods for the control and prevention of helminths with phenylbenzothiazolium compounds |
US3469009A (en) | 1964-03-16 | 1969-09-23 | Dow Chemical Co | Benzothiazolium complexes for control of parasitic organisms in animals |
GB1182008A (en) | 1966-10-03 | 1970-02-25 | Merck & Co Inc | Resolution of d1-(3-Trifluoromethylphenoxy)-(4-Chlorophenyl)Acetic Acid |
US3517051A (en) | 1964-03-20 | 1970-06-23 | Merck & Co Inc | Phenoxy substituted phenylacetic acids |
US3517050A (en) | 1966-10-03 | 1970-06-23 | Merck & Co Inc | Ester and amide derivative of (3-trifluoromethylphenoxy) (4 - halophenyl)acetic acid |
US3558778A (en) | 1966-10-27 | 1971-01-26 | Dow Chemical Co | Methods and compositions for use in animal husbandry |
US3658829A (en) | 1969-08-01 | 1972-04-25 | Sumitomo Chemical Co | Phenoxy carboxylic acid derivatives |
US3674836A (en) | 1968-05-21 | 1972-07-04 | Parke Davis & Co | 2,2-dimethyl-{11 -aryloxy-alkanoic acids and salts and esters thereof |
US3860628A (en) | 1972-07-13 | 1975-01-14 | Merck & Co Inc | Cyanomethyl(3-trifluoromethylphenoxy)(4-chlorophenyl)acetate |
US3876791A (en) | 1973-11-30 | 1975-04-08 | Uniroyal Inc | Control of acarids using certain benzothiazoles or benzothiazolines |
CA967978A (en) | 1970-10-30 | 1975-05-20 | George G. Hazen | Preparation of a hypocholesterolemic |
GB1403309A (en) | 1972-07-28 | 1975-08-28 | Merck & Co Inc | Preparation of a trifluoromethyl phenoxyacetic acid ester |
US3923855A (en) | 1972-07-13 | 1975-12-02 | Merck & Co Inc | 2-sulfonyloxyethyl 3-trifluoromethylphenoxy-4{40 -chlorophenyl acetate |
US3953490A (en) | 1972-07-13 | 1976-04-27 | Merck & Co., Inc. | Preparation of (3-trifluoromethylphenoxy)(4-chlorophenyl)acetonitrile |
US4001268A (en) | 1974-08-07 | 1977-01-04 | The United States Of America As Represented By The Secretary Of The Air Force | Substituted phenyl-benzimidazo compounds |
US4067996A (en) | 1974-12-30 | 1978-01-10 | Synthelabo | Phenylacetic acid derivatives |
JPS5315325A (en) | 1976-07-28 | 1978-02-13 | Fujisawa Pharmaceut Co Ltd | N-substituted phenylamino fatty acid derivatives |
JPS5371071A (en) | 1976-12-08 | 1978-06-24 | Teijin Ltd | Alpha-phenoxyacetic acid derivs. |
US4146623A (en) | 1973-04-02 | 1979-03-27 | Richardson-Merrell Inc. | Hypolipidemic composition and method of use |
US4214095A (en) | 1979-01-25 | 1980-07-22 | Siegfried Aktiengesellschaft | Chlorobenzyl phenoxy alkoxylates |
US4250191A (en) | 1978-11-30 | 1981-02-10 | Edwards K David | Preventing renal failure |
US4338330A (en) | 1979-05-04 | 1982-07-06 | Continental Pharma | Benzimidazole derivatives, their use, and compositions containing these derivatives |
EP0077938A2 (en) | 1981-10-23 | 1983-05-04 | Mitsubishi Kasei Corporation | N-(3-substituted aminophenyl) tetrahydrophthalimides and herbicidal composition |
EP0105494A2 (de) | 1982-10-04 | 1984-04-18 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Benzthiazolyloxyphenoxypropionsäurederivaten |
US4508882A (en) | 1981-08-24 | 1985-04-02 | Asahi Glass Company Ltd. | Benzotriazole compound and homopolymer or copolymers thereof |
JPS60109578A (ja) | 1983-11-17 | 1985-06-15 | Mitsubishi Chem Ind Ltd | 3−(置換フエニル)−5−置換−1,3,4−オキサゾリン−2−オン類およびこれを有効成分とする除草剤 |
US4528311A (en) | 1983-07-11 | 1985-07-09 | Iolab Corporation | Ultraviolet absorbing polymers comprising 2-hydroxy-5-acrylyloxyphenyl-2H-benzotriazoles |
US4532135A (en) | 1981-02-09 | 1985-07-30 | Edwards K David G | Renoprotective treatments employing vasodilator compounds |
US4714762A (en) | 1986-10-31 | 1987-12-22 | Warner-Lambert Company | Antiarteriosclerotic substituted benzimidazol-2-yl-and 3H-imidazo[4,5-b]pyridin-2-yl-phenoxy-alkanoic acids and salts and esters thereof |
US4786731A (en) | 1987-08-05 | 1988-11-22 | The Dow Chemical Company | Resolution of enantiomers of 2-(phenyl or phenoxy/propionic acids using optically active alkanolamines |
EP0306708A1 (en) | 1987-08-07 | 1989-03-15 | Kanebo, Ltd. | Novel benzothiazole and antirheumatic agent comprising it as an active ingredient |
US4863802A (en) | 1987-12-31 | 1989-09-05 | General Electric Company | UV-stabilized coatings |
US4891396A (en) | 1987-08-28 | 1990-01-02 | Sandoz Ltd. | New benztriazolyl compounds |
US4933367A (en) | 1985-07-16 | 1990-06-12 | Boehringer Mannheim Gmbh | Carboxylic acid derivatives, processes for the preparation thereof, the use thereof, and pharmaceutical compositions which contain these compounds |
US5132429A (en) | 1988-05-31 | 1992-07-21 | Shionogi & Co., Ltd. | Benzotriazole derivatives and fluorescence-emitting reagents thereof |
WO1992017435A1 (de) | 1991-04-05 | 1992-10-15 | Boehringer Mannheim Gmbh | Optisch aktive carbonsäuren sowie diese enthaltende arzneimittel |
US5284599A (en) | 1990-01-22 | 1994-02-08 | Canon Kabushiki Kaisha | Mesomorphic compound, liquid crystal composition containing same, liquid crystal device using same display apparatus |
US5476946A (en) | 1993-02-09 | 1995-12-19 | Bayer Aktiengesellschaft | 1-aryltriazolin(ethi)ones |
US5496826A (en) | 1994-09-02 | 1996-03-05 | Bristol-Myers Squibb Company | Pharmaceutical methods of using heterocyclic derivatives of N-phenylamides |
US5500332A (en) | 1995-04-26 | 1996-03-19 | Eastman Kodak Company | Benzotriazole based UV absorbers and photographic elements containing them |
US5516914A (en) | 1991-02-12 | 1996-05-14 | Ciba-Geigy Corporation | Compositions stabilized with 5-thio-substituted benzotriazole UV-absorbers |
US5554759A (en) | 1994-09-27 | 1996-09-10 | Eastman Kodak Company | Benzotriazole based uv absorbing monomers and photographic elements containg polymers formed them |
US5700819A (en) | 1994-11-29 | 1997-12-23 | Grelan Pharmaceutical Co., Ltd. | 2-substituted benzothiazole derivatives and prophylactic and therapeutic agents for the treatment of diabetic complications |
US5716987A (en) | 1996-06-21 | 1998-02-10 | Bristol-Myers Squibb Company | Prophylactic and therapeutic treatment of skin sensitization and irritation |
WO1998023252A1 (en) | 1996-11-22 | 1998-06-04 | Ciba Specialty Chemicals Holding Inc. | Use of selected benzotriazole derivatives for protecting human and animal skin and hair from the harmful effects of uv radiation |
US5766834A (en) | 1996-05-17 | 1998-06-16 | Eastman Kodak Company | Photographic element containing ultraviolet absorbing polymer |
US5859051A (en) | 1996-02-02 | 1999-01-12 | Merck & Co., Inc. | Antidiabetic agents |
US5874431A (en) | 1993-08-28 | 1999-02-23 | Cancer Research Campaign Technology Limited | Benzazole compounds |
WO1999011627A1 (en) | 1997-09-05 | 1999-03-11 | Ortho-Mcneil Pharmaceutical, Inc. | 2-substituted phenyl-benzimidazole antibacterial agents |
US5883124A (en) | 1991-10-21 | 1999-03-16 | The United States Of America As Represented By The Department Of Health And Human Services | Compositions and methods for treating and preventing pathologies including cancer |
US6013659A (en) | 1998-09-04 | 2000-01-11 | University Of Pittsburgh | Methods of reducing tumor colony number using novel benzothiazole compounds |
US6034246A (en) | 1995-02-28 | 2000-03-07 | Cancer Research Campaign Technology Limited | 2-arylbenzazole compounds |
US6037493A (en) | 1994-12-28 | 2000-03-14 | Rhone-Poulenc Chimie | Optically active diphosphines, preparation thereof according to a process for the resolution of the racemic mixture and use thereof |
US6069272A (en) | 1992-03-09 | 2000-05-30 | Hoechst Aktiengesellschaft | Simplified method for the production of vinyl glycine (2-aminobut-3-enoic acid) and a convenient resolution of a derivative |
WO2000035886A2 (en) | 1998-12-18 | 2000-06-22 | Axys Pharmaceuticals, Inc. | (hetero)aryl-bicyclic heteroaryl derivatives, their preparation and their use as protease inhibitors |
US6093830A (en) | 1998-11-09 | 2000-07-25 | Council Of Scientific And Industrial Research | Enantioselective resolution process for arylpropionic acid drugs from the racemic mixture |
WO2000074666A2 (en) | 1999-06-04 | 2000-12-14 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes, hyperlipidaemia and hyperuricaemia |
US6184235B1 (en) | 1996-08-14 | 2001-02-06 | Warner-Lambert Company | 2-phenyl benzimidazole derivatives as MCP-1 antagonists |
US6201147B1 (en) | 1998-09-30 | 2001-03-13 | Basf Aktiengesellschaft | Process for the resolution of esters of arylalkylcarboxylic acids |
US6242464B1 (en) | 1996-01-22 | 2001-06-05 | Chiroscience Limited | Single isomer methylphenidate and resolution process |
US6248768B1 (en) | 1997-11-07 | 2001-06-19 | Taiho Pharmaceutical Co., Ltd. | Benzimidazole derivatives and pharmacologically acceptable salts thereof |
EP1162196A1 (en) | 1999-12-27 | 2001-12-12 | Japan Tobacco Inc. | Fused-ring compounds and use thereof as drugs |
WO2002044113A2 (en) | 2000-11-28 | 2002-06-06 | Metabolex, Inc. | Use of(-) (3-halomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes, hyperlipidemia and hyperuricemia |
US6506747B1 (en) | 1998-06-05 | 2003-01-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents |
US20030220399A1 (en) | 1999-06-04 | 2003-11-27 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, Type 2 diabetes, hyperlipidemia and hyperuricemia |
US20040204472A1 (en) | 2003-03-04 | 2004-10-14 | Pharmacia Corporation | Treatment and prevention of obesity with COX-2 inhibitors alone or in combination with weight-loss agents |
WO2004112774A1 (en) | 2003-06-20 | 2004-12-29 | Metabolex, Inc. | RESOLUTION OF α-(PHENOXY)PHENYLACETIC ACID DERIVATIVES |
US20050033084A1 (en) | 2003-06-20 | 2005-02-10 | Metabolex, Inc. | Resolution of alpha-(phenoxy)phenylacetic acid derivatives |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5708186A (en) * | 1995-12-12 | 1998-01-13 | Merck & Co Inc | Stereoselective process |
-
2006
- 2006-09-20 US US11/525,200 patent/US7714131B2/en not_active Expired - Fee Related
- 2006-09-21 AU AU2006294950A patent/AU2006294950A1/en not_active Abandoned
- 2006-09-21 EA EA200800884A patent/EA015673B1/ru not_active IP Right Cessation
- 2006-09-21 BR BRPI0616188-0A patent/BRPI0616188A2/pt not_active IP Right Cessation
- 2006-09-21 SI SI200631502T patent/SI1940387T1/sl unknown
- 2006-09-21 PT PT68151505T patent/PT1940387E/pt unknown
- 2006-09-21 CA CA2623350A patent/CA2623350C/en not_active Expired - Fee Related
- 2006-09-21 WO PCT/US2006/036928 patent/WO2007038243A1/en active Application Filing
- 2006-09-21 DK DK06815150.5T patent/DK1940387T3/da active
- 2006-09-21 PL PL06815150T patent/PL1940387T3/pl unknown
- 2006-09-21 ES ES06815150T patent/ES2394973T3/es active Active
- 2006-09-21 KR KR1020087009709A patent/KR101309605B1/ko not_active IP Right Cessation
- 2006-09-21 JP JP2008532404A patent/JP2009515817A/ja not_active Withdrawn
- 2006-09-21 RS RS20130001A patent/RS52608B/en unknown
- 2006-09-21 EP EP06815150A patent/EP1940387B1/en active Active
-
2008
- 2008-03-20 IL IL190325A patent/IL190325A/en not_active IP Right Cessation
- 2008-12-29 HK HK08114045.8A patent/HK1119953A1/xx not_active IP Right Cessation
-
2013
- 2013-01-02 HR HRP20130001TT patent/HRP20130001T1/hr unknown
Patent Citations (81)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3444299A (en) | 1964-02-07 | 1969-05-13 | American Cyanamid Co | Methods for the control and prevention of helminths with phenylbenzothiazolium compounds |
US3469009A (en) | 1964-03-16 | 1969-09-23 | Dow Chemical Co | Benzothiazolium complexes for control of parasitic organisms in animals |
US3378582A (en) | 1964-03-20 | 1968-04-16 | Merck & Co Inc | (alpha-phenoxy)-and (alpha-phenylthio)-omegaphenyl-alkanoic acids |
US3517051A (en) | 1964-03-20 | 1970-06-23 | Merck & Co Inc | Phenoxy substituted phenylacetic acids |
FR1476525A (fr) | 1964-03-20 | 1967-04-14 | Merck & Co Inc | Nouveaux acides alkanoïques à substituant aryle et procédés pour leur préparation |
GB1182008A (en) | 1966-10-03 | 1970-02-25 | Merck & Co Inc | Resolution of d1-(3-Trifluoromethylphenoxy)-(4-Chlorophenyl)Acetic Acid |
US3517050A (en) | 1966-10-03 | 1970-06-23 | Merck & Co Inc | Ester and amide derivative of (3-trifluoromethylphenoxy) (4 - halophenyl)acetic acid |
US3558778A (en) | 1966-10-27 | 1971-01-26 | Dow Chemical Co | Methods and compositions for use in animal husbandry |
US3674836A (en) | 1968-05-21 | 1972-07-04 | Parke Davis & Co | 2,2-dimethyl-{11 -aryloxy-alkanoic acids and salts and esters thereof |
US3658829A (en) | 1969-08-01 | 1972-04-25 | Sumitomo Chemical Co | Phenoxy carboxylic acid derivatives |
CA967978A (en) | 1970-10-30 | 1975-05-20 | George G. Hazen | Preparation of a hypocholesterolemic |
US3860628A (en) | 1972-07-13 | 1975-01-14 | Merck & Co Inc | Cyanomethyl(3-trifluoromethylphenoxy)(4-chlorophenyl)acetate |
US3923855A (en) | 1972-07-13 | 1975-12-02 | Merck & Co Inc | 2-sulfonyloxyethyl 3-trifluoromethylphenoxy-4{40 -chlorophenyl acetate |
US3953490A (en) | 1972-07-13 | 1976-04-27 | Merck & Co., Inc. | Preparation of (3-trifluoromethylphenoxy)(4-chlorophenyl)acetonitrile |
GB1403309A (en) | 1972-07-28 | 1975-08-28 | Merck & Co Inc | Preparation of a trifluoromethyl phenoxyacetic acid ester |
US4146623A (en) | 1973-04-02 | 1979-03-27 | Richardson-Merrell Inc. | Hypolipidemic composition and method of use |
US3876791A (en) | 1973-11-30 | 1975-04-08 | Uniroyal Inc | Control of acarids using certain benzothiazoles or benzothiazolines |
US4001268A (en) | 1974-08-07 | 1977-01-04 | The United States Of America As Represented By The Secretary Of The Air Force | Substituted phenyl-benzimidazo compounds |
US4067996A (en) | 1974-12-30 | 1978-01-10 | Synthelabo | Phenylacetic acid derivatives |
JPS5315325A (en) | 1976-07-28 | 1978-02-13 | Fujisawa Pharmaceut Co Ltd | N-substituted phenylamino fatty acid derivatives |
JPS5371071A (en) | 1976-12-08 | 1978-06-24 | Teijin Ltd | Alpha-phenoxyacetic acid derivs. |
US4250191A (en) | 1978-11-30 | 1981-02-10 | Edwards K David | Preventing renal failure |
US4214095A (en) | 1979-01-25 | 1980-07-22 | Siegfried Aktiengesellschaft | Chlorobenzyl phenoxy alkoxylates |
US4338330A (en) | 1979-05-04 | 1982-07-06 | Continental Pharma | Benzimidazole derivatives, their use, and compositions containing these derivatives |
US4532135A (en) | 1981-02-09 | 1985-07-30 | Edwards K David G | Renoprotective treatments employing vasodilator compounds |
US4508882A (en) | 1981-08-24 | 1985-04-02 | Asahi Glass Company Ltd. | Benzotriazole compound and homopolymer or copolymers thereof |
EP0077938A2 (en) | 1981-10-23 | 1983-05-04 | Mitsubishi Kasei Corporation | N-(3-substituted aminophenyl) tetrahydrophthalimides and herbicidal composition |
EP0105494A2 (de) | 1982-10-04 | 1984-04-18 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Benzthiazolyloxyphenoxypropionsäurederivaten |
US4528311A (en) | 1983-07-11 | 1985-07-09 | Iolab Corporation | Ultraviolet absorbing polymers comprising 2-hydroxy-5-acrylyloxyphenyl-2H-benzotriazoles |
JPS60109578A (ja) | 1983-11-17 | 1985-06-15 | Mitsubishi Chem Ind Ltd | 3−(置換フエニル)−5−置換−1,3,4−オキサゾリン−2−オン類およびこれを有効成分とする除草剤 |
US4933367A (en) | 1985-07-16 | 1990-06-12 | Boehringer Mannheim Gmbh | Carboxylic acid derivatives, processes for the preparation thereof, the use thereof, and pharmaceutical compositions which contain these compounds |
US4714762A (en) | 1986-10-31 | 1987-12-22 | Warner-Lambert Company | Antiarteriosclerotic substituted benzimidazol-2-yl-and 3H-imidazo[4,5-b]pyridin-2-yl-phenoxy-alkanoic acids and salts and esters thereof |
US4786731A (en) | 1987-08-05 | 1988-11-22 | The Dow Chemical Company | Resolution of enantiomers of 2-(phenyl or phenoxy/propionic acids using optically active alkanolamines |
EP0306708A1 (en) | 1987-08-07 | 1989-03-15 | Kanebo, Ltd. | Novel benzothiazole and antirheumatic agent comprising it as an active ingredient |
US4910211A (en) | 1987-08-07 | 1990-03-20 | Kanebo Ltd. | Novel benzothiazole and antirheumatic agent comprising it as an active ingredient |
US4891396A (en) | 1987-08-28 | 1990-01-02 | Sandoz Ltd. | New benztriazolyl compounds |
US4863802A (en) | 1987-12-31 | 1989-09-05 | General Electric Company | UV-stabilized coatings |
US5132429A (en) | 1988-05-31 | 1992-07-21 | Shionogi & Co., Ltd. | Benzotriazole derivatives and fluorescence-emitting reagents thereof |
US5284599A (en) | 1990-01-22 | 1994-02-08 | Canon Kabushiki Kaisha | Mesomorphic compound, liquid crystal composition containing same, liquid crystal device using same display apparatus |
US5942626A (en) | 1991-02-12 | 1999-08-24 | Ciba Specialty Chemicals Corporation | Process for making 5-thio-substituted benzotriazole UV absorbers |
US5516914A (en) | 1991-02-12 | 1996-05-14 | Ciba-Geigy Corporation | Compositions stabilized with 5-thio-substituted benzotriazole UV-absorbers |
WO1992017435A1 (de) | 1991-04-05 | 1992-10-15 | Boehringer Mannheim Gmbh | Optisch aktive carbonsäuren sowie diese enthaltende arzneimittel |
US5883124A (en) | 1991-10-21 | 1999-03-16 | The United States Of America As Represented By The Department Of Health And Human Services | Compositions and methods for treating and preventing pathologies including cancer |
US6069272A (en) | 1992-03-09 | 2000-05-30 | Hoechst Aktiengesellschaft | Simplified method for the production of vinyl glycine (2-aminobut-3-enoic acid) and a convenient resolution of a derivative |
US5476946A (en) | 1993-02-09 | 1995-12-19 | Bayer Aktiengesellschaft | 1-aryltriazolin(ethi)ones |
US5874431A (en) | 1993-08-28 | 1999-02-23 | Cancer Research Campaign Technology Limited | Benzazole compounds |
US5496826A (en) | 1994-09-02 | 1996-03-05 | Bristol-Myers Squibb Company | Pharmaceutical methods of using heterocyclic derivatives of N-phenylamides |
US5554759A (en) | 1994-09-27 | 1996-09-10 | Eastman Kodak Company | Benzotriazole based uv absorbing monomers and photographic elements containg polymers formed them |
US5700819A (en) | 1994-11-29 | 1997-12-23 | Grelan Pharmaceutical Co., Ltd. | 2-substituted benzothiazole derivatives and prophylactic and therapeutic agents for the treatment of diabetic complications |
US6037493A (en) | 1994-12-28 | 2000-03-14 | Rhone-Poulenc Chimie | Optically active diphosphines, preparation thereof according to a process for the resolution of the racemic mixture and use thereof |
US6034246A (en) | 1995-02-28 | 2000-03-07 | Cancer Research Campaign Technology Limited | 2-arylbenzazole compounds |
US5500332A (en) | 1995-04-26 | 1996-03-19 | Eastman Kodak Company | Benzotriazole based UV absorbers and photographic elements containing them |
US6242464B1 (en) | 1996-01-22 | 2001-06-05 | Chiroscience Limited | Single isomer methylphenidate and resolution process |
US5859051A (en) | 1996-02-02 | 1999-01-12 | Merck & Co., Inc. | Antidiabetic agents |
US5766834A (en) | 1996-05-17 | 1998-06-16 | Eastman Kodak Company | Photographic element containing ultraviolet absorbing polymer |
US6670395B1 (en) | 1996-06-21 | 2003-12-30 | Bristol-Myers Squibb Company | Prophylactic and therapeutic treatment of skin sensitization and irritation |
US5716987A (en) | 1996-06-21 | 1998-02-10 | Bristol-Myers Squibb Company | Prophylactic and therapeutic treatment of skin sensitization and irritation |
US6184235B1 (en) | 1996-08-14 | 2001-02-06 | Warner-Lambert Company | 2-phenyl benzimidazole derivatives as MCP-1 antagonists |
WO1998023252A1 (en) | 1996-11-22 | 1998-06-04 | Ciba Specialty Chemicals Holding Inc. | Use of selected benzotriazole derivatives for protecting human and animal skin and hair from the harmful effects of uv radiation |
US6201000B1 (en) | 1996-11-22 | 2001-03-13 | Ciba Specialty Chemicals Corporation | Use of selected benzotriazole derivatives for protecting human and animal skin and hair from the harmful effects of UV radiation |
WO1999011627A1 (en) | 1997-09-05 | 1999-03-11 | Ortho-Mcneil Pharmaceutical, Inc. | 2-substituted phenyl-benzimidazole antibacterial agents |
US6248768B1 (en) | 1997-11-07 | 2001-06-19 | Taiho Pharmaceutical Co., Ltd. | Benzimidazole derivatives and pharmacologically acceptable salts thereof |
US6506747B1 (en) | 1998-06-05 | 2003-01-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents |
US6013659A (en) | 1998-09-04 | 2000-01-11 | University Of Pittsburgh | Methods of reducing tumor colony number using novel benzothiazole compounds |
US6201147B1 (en) | 1998-09-30 | 2001-03-13 | Basf Aktiengesellschaft | Process for the resolution of esters of arylalkylcarboxylic acids |
US6093830A (en) | 1998-11-09 | 2000-07-25 | Council Of Scientific And Industrial Research | Enantioselective resolution process for arylpropionic acid drugs from the racemic mixture |
WO2000035886A2 (en) | 1998-12-18 | 2000-06-22 | Axys Pharmaceuticals, Inc. | (hetero)aryl-bicyclic heteroaryl derivatives, their preparation and their use as protease inhibitors |
US20030220399A1 (en) | 1999-06-04 | 2003-11-27 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, Type 2 diabetes, hyperlipidemia and hyperuricemia |
US6262118B1 (en) | 1999-06-04 | 2001-07-17 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes and hyperlipidemia |
US20050075396A1 (en) | 1999-06-04 | 2005-04-07 | Metabolex, Inc. | Use of (-)(3-trihalomethylphenoxy)(4-halophenyl) acetic acid derivatives for treatment of insulin resistance, Type 2 diabetes and hyperlipidemia |
US6613802B1 (en) | 1999-06-04 | 2003-09-02 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes, hyperlipidemia and hyperuricemia |
US6624194B1 (en) | 1999-06-04 | 2003-09-23 | Metabolex, Inc. | Use of (−) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes, hyperlipidemia and hyperuricemia |
US6646004B1 (en) | 1999-06-04 | 2003-11-11 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes and hyperlipidemia |
WO2000074666A2 (en) | 1999-06-04 | 2000-12-14 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes, hyperlipidaemia and hyperuricaemia |
EP1162196A1 (en) | 1999-12-27 | 2001-12-12 | Japan Tobacco Inc. | Fused-ring compounds and use thereof as drugs |
WO2002044113A2 (en) | 2000-11-28 | 2002-06-06 | Metabolex, Inc. | Use of(-) (3-halomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes, hyperlipidemia and hyperuricemia |
US20040039053A1 (en) | 2000-11-28 | 2004-02-26 | Luskey Kenneth L. | Use of(-) (3-halomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes, hyperlipidemia and hyperuricemia |
US20040204472A1 (en) | 2003-03-04 | 2004-10-14 | Pharmacia Corporation | Treatment and prevention of obesity with COX-2 inhibitors alone or in combination with weight-loss agents |
WO2004112774A1 (en) | 2003-06-20 | 2004-12-29 | Metabolex, Inc. | RESOLUTION OF α-(PHENOXY)PHENYLACETIC ACID DERIVATIVES |
US20050033084A1 (en) | 2003-06-20 | 2005-02-10 | Metabolex, Inc. | Resolution of alpha-(phenoxy)phenylacetic acid derivatives |
US7199259B2 (en) | 2003-06-20 | 2007-04-03 | Metabolex, Inc. | Resolution of α-(phenoxy)phenylacetic acid derivatives |
Non-Patent Citations (84)
Title |
---|
Aronow, W.S. et al., "Effect of Halofenate on Serum Uric Acid," Clin. Pharmacol. Ther., 1973, vol. 14, No. 3, pp. 371-373. |
Aronow, W.S. et al., "Halofenate: An Effective Hypolipemia- and Hypouricemia-Inducing Drug," Current Therapeutic Research, 1973, vol. 15, No. 12, pp. 902-906. |
Bardin, C.W. ed., Current Therapy in Endocrinology and Metabolism 6th Edition, Mosby-Year Book, Inc., St. Louis: MO, 1997, pp. 509-519 |
Barrett-Conner, O.E., "Epidemology, Obesity, and Mellitus", Epidemol. Rev.,1989, vol. 11, pp. 172-181. |
Bassett, D.R. et al., "Effects of Halofenate and Probenecid in Serum Lipids and Uric Acid in Hyperlipidemic, Hyperuricemic Adults," Clin. Pharmacol. Ther. 1977, vol. 22, No. 3, pp. 340-351. |
Bell, G.I. et al., "Glucokinase Mutations, Insulin Secretion, and Diabetes Mellitus," Annu. Rev. Physiol., 1996, vol. 58, No. pp. 171-187. |
Berkow, R. et al. eds., "Disorders of Carbohydrate Metabolism," Chapter 94 In The Merck Manual of Diagnosis and Therapy 15th ed., Merck Sharp & Dohme Research Laboratories, 1987, pp. 1069-1072. |
Bluestone, R. et al., "Halofenate its Selection and Trial as a Primary Uricosuric Agent," Arthritis Rheum., 1975, vol. 18, pp. 859-862. |
Brooks, D.A. et al., "Design and Synthesis of 2-Methyl-2-4{4-{2-(5-methyl-2-aryloxazol-4-yl)ethoxy}phenoxy-propionic Acids: A New Class of Dual PPARalpha/y Agonists," J. Med. Chem., Dec. 15, 2001, vol. 44, pp. 2061-2064. |
Brooks, D.A. et al., "Design and Synthesis of 2-Methyl-2-4{4-{2-(5-methyl-2-aryloxazol-4-yl)ethoxy}phenoxy-propionic Acids: A New Class of Dual PPARα/y Agonists," J. Med. Chem., Dec. 15, 2001, vol. 44, pp. 2061-2064. |
Chiasson, J-L. et al., "The Efficacy of Acarbose in the Treatment of Patients With Non-Insulin-Dependant Diabetes Mellitus," Annals of Intern. Med., 1994 vol. 121, No. 12, pp. 928-935. |
Coniff, R. et al., "Acarbose: a Review of US Clinical Experience," Clinical Therapeutics, 1997, vol. 19, No. 1, pp. 16-26. |
Coniff, R.F et al., "Multicenter, Placebo-Controlled Trial Comparing Acarbose (BAY g 5421) With Placebo, Tolbutamide, and Tolbutamide-Plus-Acarbose in Non-Insulin-Dependent Diabetes Mellitus," The American Journal of Medicine, May 1995, vol. 98, pp. 443-451. |
Devine et al. Tetrahedron Letters 1996, 37(16), 2683-2686. * |
Devine, P.N., "Stereoselective Synthesis of 2-Aryloxy Esters: an Asymmetric Approach to Fluoxetine, Tomoxetine and Nisoxetine," Tetrahedron, 1997, vol. 53, No. 20, pp. 6739-6746. |
Diamant, M. et al., "Thiazolidinediones in Type 2 Diabetes Mellitus: Current Clinical Evidence," Drugs, 2003, vol. 63, No. 13, pp. 1373-1405, Abstract. |
Dörfler, H. et al., "Primärer Verteilungsraum and Plasmahalbwertszeit von Intravenös Verbreichtem Insulin," Med. Poliklinik Univ. Muchen, 1973, pp. 1297-1299. |
Edelman, S.V. et al., "Non-Insulin-Dependent Diabetes Mellitus", In Current Therapy in Endocrinology and Metabolism Sixth Edition, 1997, pp. 430-438. |
El-Sherief, H.A. et al., "Synthesis and Antimicrobial Activities of Some New Benzimidazoles, Part I," Bull. Fac. Sci. Assiut Univ. B, 1995, vol. 24, No. 1, pp. 111-123. |
Fajans, S.S. et al., "Maturity Obset Diabetes of the Young (MODY)" Diabetes Medicine, 1996, vol. 13, pp. S90-S95. |
Fanelli, G.M., Jr. et al., "Renal Excretion and Uricosuric Properties of Halofenate A Hypolipidemic Uricosuric Agent in the Chimpanzee," J. Pharmacol. Exp. Ther., 1972, vol. 180, pp. 377-396. |
Feldman, E.B. et al., "Effects of Halofenate on Glucose Tolerance in Patients with Hyperlipoproteinemia," Journal Clinical Pharmacology, May-Jun. 1978, vol. 18, pp. 241-248. |
Feldman, E.B. et al., "Insulin Sensitivity in Hypertriglyceridemia: Induction by Combined Triglyceride and Uric Acid Lowering," Clinical Research, Jan. 1975, vol. 23, No. 1, p. 43A. |
Flier, J.S., "Insulin Receptors and Insulin Resistance," Ann Rev. Med., 1983, vol. 34, pp. 145-160. |
Friedberg, S.J., "The Control of Insulin Resistant and Refractory Type II Diabetes Mellitus by Means of Halofenate-Sulfonylurea Combined Regimen," Clinical Research, 1986, vol. 34, p. 682A. |
Gavin III, J.R. et al., "Report of the Expert Committee on the Diagnosis and Classification of Diabetes Mellitus," Diabetes Care, Jan. 1999, vol. 22, Supplement 1, pp. S5-S19. |
Goetze, S., et al., "PPARgamma-Ligands Inhibit Migration Mediated by Multiple Chemoattractants in Vascular Smooth Muscle Cells," Journal of Cardiovascular Pharmacology, 1999, vol. 33, pp. 798-806. |
Goetze, S., et al., "PPARγ-Ligands Inhibit Migration Mediated by Multiple Chemoattractants in Vascular Smooth Muscle Cells," Journal of Cardiovascular Pharmacology, 1999, vol. 33, pp. 798-806. |
Harpp et al. J. Org. Chem. 1975, 40, 3420. * |
Howard, B.V., et al., "Lipoprotein Composition in Diabetes Mellitus," Atherosclerosis, 1978, vol. 30, pp. 153-162. |
Huang, X. et al., "Search for New Antiphytovirucides," J. Wuhan Univ. (Nature Science Edition), Apr. 1995, vol. 41, No. 2, pp. 142-148. |
Hucker, H.B. et al., "Metabolism of a New Hypolipidemic Agent, 2-Acetamidoethyl (p-Chlorophenyl) (m-Trifluoromethylphenoxy)-Acetate (Halofenate) in the Rat, Dog, Rhesus Monkey and Man," The Journal of Pharmacology and Experimental Therapeutics, 1971, vol. 179, No. 2, pp. 359-371. |
Hutchison, J.C. et al., "The Uricosuric Action of Halofenate (MK-185) in Patients with Hyperuricemia or Uncomplicated Primary Gout and Hyperlipidemia," Atherosclerosis, 1973, vol. 18, pp. 353-362. |
International Search Report mailed Feb. 16, 2007, for PCT Application No. PCT/US06/36928 filed on Sep. 21, 2006, two pages. |
Iwamoto, Y. et al., "Effect of Combination Therapy of Troglitazone and Sulphonylureas in Patients with Type 2 Diabetes Who Were Poorly Contorlled by Sulphonylurea Therapy Alone," Diabetic Medicine, 1996, vol. 13, pp. 365-370. |
Jacques, J. et al., "Formation and Separation of Diasteromers." In Enantiomers, Racemates, and Resolutions, John Wiley & Sons, New York, 1981, pp. 251-328. |
Jain, A. et al., "Potentiation of Hypoglycemic Effect of Sulfonylureas by Halofenate," New England J. of Med., Dec. 15, 1975, vol. 293, No. 25, pp. 1283-1286. |
Jain, A. et al., "The Effect of MK-185 on Some Aspects of Uric Acid Metabolism," Clin. Pharmacol. Ther., Jul.-Aug. 1970, vol. 11, pp. 551-557. |
Joslin, E.P., "Arteriosclerosis and Diabetes," Annals of Clinical Medicine, 1927, vol. 5, No. 12, pp. 1061-1079. |
Keller, V.C. et al., "Die Benhandlung von Hyperlipidämie und Hyperurikärnie mit 2-Acetamidoäthyl-(4-chlorophenyI)-(3-trifluoromethylphenoxy)-acetat (Halofenat), einem Derivat des Clofibrat," Arzneimittelforschung, 1976, vol. 26, No. 12, pp. 2221-2224. |
Knowler, W.C. et al., "Obesity in the Pima Indians: its magnitude and relationship with diabetes," Am. J. Clin. Nutr., 1991, vol. 53, pp. 1543S-1551S. |
Kobayashi, M., et al., "Improvement of Glucose Tolerance in NIDDM by Clofibrate Randomized Double-Blind Study," Diabetes Care, Jun. 1988, vol. 11, No. 6, pp. 495-499. |
Kohl, E.A. et al., "Improved Control of Non-Insulin-Dependent Diabetes Mellitus by Combined Halofenate and Chlorpropamide Therapy," Diabetes Care, Jan.-Feb. 1984 vol. 7, No. 1, pp. 19-24. |
Kreisberg, R.A., "Hyperlipidemia," Current Therapy in Endocrinology and Metabolism 6th Edition, 1997, pp. 509-519. |
Krut, L.H. et al., "Comparison of Clofibrate with Halofenate in Diabetics with Hyperlipidaemia," S.A. Med. J., 1977, pp. 348-352. |
Kudzma, D.J. et al., "Potentiation of Hypoglycemic Effect of Chlorpropamide and Phenformin by Halofenate," Diabetes, Apr. 1977, vol. 26, No. 4, pp. 291-295. |
Kuntznen V.O. et al., "Wirkung von Halofenat auf Triglycerid-und Harnsäurespiegel sowie auf Gerinnungsund Thrombozytenverhalten bei Patienten mit Hyperlipoproteinämie Typ IV und Hyperurikämie," Arzneimittelforschung, 1978, vol. 28, No. 12, pp. 2349-2352. |
Kwiterovich, P. Jr., "State-of-the-Art Update and Review: Clinical Trials of Lipid-Lowering Agents," The American Journal of Cardiology, Dec. 1998, vol. 82, No. 12A, pp. 3U-17U. |
Leroith, D. et al. eds., Diabetes Mellitus, Lippincott-Raven Publishers, Philadelphia: PA, 1996. (Table of Contents Only). |
Lin, J.H. et al., "Inhibition and Induction of Cytochrome P450 and the Clinical Implications," Clin Pharmacokinet, Nov. 1998, vol. 35, No. 5, pp. 361-390. |
Lisch, H.-J. et al., "Comparison of the Effects of Halofenate (MK-185) and Clofibrate on Plasma Lipid and Uric Acid Concentration in Hyperlipoproteinemic Patients," Atheroschlerosis, 1995, vol. 21, pp. 391-399. |
Lochmüller, C.H. et al., "Chromatographic Resolution of Enantiomers." J. Chromatography, 1975, vol. 113, pp. 283-302. |
Mahley, R.W. et al., "Disorders of Lipid Metabolism," Chapter 23 In Williams Textbook of Endocrinology 9th Edition, 1998, W.B. Sanders Company, Philadelphia: PA, pp. 1099-1153. |
Malher, R.J., Clinical Review 102, "Type 2 Diabetes Mellitus: Update on Diagnosis, Pathophysiology, and Treatment," J. Clin. Endocrinol. Metab., 1999, vol. 84, No. 4, pp. 1165-1171. |
Mandel, L.R., "Studies on the Mechanism of Action of Halofenate," Lipids, 1976, vol. 12, No. 1, pp. 34-43. |
McMahon, F.G. et al., "Some Effects of MK-185 on Lipid and Uric Acid Metabolism in Man," Univ. Mich. Med. Center J., Oct.-Dec. 1970, vol. 36, No. 4, pp. 247-248. |
Metabolex, The Diabetes Biopharmaceutical Company, "Metabolic Disease Drug Discovery & Development Summit," Strategic Research Institute, (May 6-7, 2002). |
Miners, J.O. et al., "Cytochrome P4502C9: An Enzyme of Major Importance in Human Drug Metabolism," J Clin Pharmacol, 1998, vol. 45, pp. 525-538. |
Morgan, J.P. et al., "Hypolipidemic, Uricosuric, and Thyroxine-displacing Effects of MK-185 (halofenate)," Clin. Pharmacol. Therap., 1971, vol. 12, No. 3, pp. 517-524. |
Neuman, J., et al., "A Double-Blind Comparison of the Hypolipidemic and Hypouricemic Action of Halofenate and Clofibrate in Patients with Hyperlipoprteinemia," The International Cardiovascular Society, pp. 532-537, 1973. |
Pelkonen, O. et al., "Inhibition and Induction of Human Cytochrome P450 (CYP) Enzymes," Xenobiotica, 1998, vol. 28, No. 12, pp. 1203-1253. |
Qu, F. et al., "Search for New Antiphytovirucides," Wuhan Univ. Journal of National Science, 1998, vol. 3, No. 2, pp. 201-204. |
Qu, F. et al., "Some New Antiphytoviral Compounds Containing Trifluoromethyl Group," Wuhan Univ. Journal of National Science, 1996, vol. 1, No. 2, pp. 283-284. |
Ravenscoft, P.J. et al., "Studies of the Uricosuric Action of the Hypolipidemic Drug Halofenate," Clin. Pharmacol. Ther., Jul.-Aug. 1973, vol. 14, No. 4, pp. 547-551. |
Read, J. et al., "The Complete Optical Resolution of Externally Compensated Acids and Bases," Journal of the Society of the Chemical Industry-London, Jan. 13, 1928, vol. 47, pp. 8T-11T. |
Reaven, G.M., "Insulin Resistance and Human Disease: A Short History," J. Basic & Clin. Phys. & Pharm., 1998, vol. 9, No. 2-4, pp. 387-406. |
Reaven, G.M., "Pathophysiology of Insulin Resistance in Human Disease," Physiol. Rev. Jul. 1995, vol. 75, No. 3, pp. 473-486. |
Ryan, J.R., "The Metabolic Spectrum of Halofenate," Int. J. Clin. Pharmacol., 1975, vol. 12, No. 1/2, pp. 239-243. |
Safak, C. et al., "Synthesis of Some Benzimidazol Derivatives, and Their Effects on Serum Total Cholesterol and Trigliceride Levels in Rats," FABAD J. Farm. Sci., 1983, vol. 8, pp. 19-29. |
Schaeffer, S. "Trying to Beat PPAR," BioCentury, The Bernstein Report on BioBusiness, (Reprint from Jun. 14, 2004), pp. 1-3. |
Schapel, G.J. et al., "Efficacy and Interactions of Oxandrolone, Halofenate and Clofibrate in a Factorial Study on Experimental Acute Nephrotic Hyperlipidemia," The Journal of Pharmacology and Experimental Therapeutics, 1975, vol. 194, No. 1, pp. 274-284. |
Schlosstein, L.H. et al. "Studies with Some Novel Uricosuric Agents and Their Metabolites: Correlation Between Clinical Activity and Drug-Induced Displacement of Urate From its Albumin-Binding Sites," J. Lab. Clin. Med., Sep. 1973, vol. 82, No. 3, pp. 412-418. |
Shi, G.Q., "Design and Synthesis of alpha-Aryloxyphenylacetic Acid Derivatives: A Novel Class of PPARalphalgamma Dual Agonists with Potent Antihyperglycemic and Lipid Modulating Activity," J. Med. Chem., 2005, vol. 48, pp. 4457-4468. |
Shi, G.Q., "Design and Synthesis of α-Aryloxyphenylacetic Acid Derivatives: A Novel Class of PPARαlγ Dual Agonists with Potent Antihyperglycemic and Lipid Modulating Activity," J. Med. Chem., 2005, vol. 48, pp. 4457-4468. |
Sirtori, C. et al., "Clinical Evaluation of MK-185: A New Hypolipidemic Drug," Lipids, 1971, vol. 7, No. 2, pp. 96-99. |
Skyler, J.S., "Glucose Control in Type 2 Diabetes Mellitus," Annals of Internal Medicine, Nov. 1, 1997, vol. 127, No. 9, pp. 837-838. |
Steiner, A., et al., "A Comparative Review of the Adverse Effects of Treatments for Hyperlipidaemia," Drug Safety, 1991, vol. 6, No. 2, pp. 118-130. |
Taskinen, M.-R., "Lipid Disorders in NIDDM: Implications for Treatment," Journal of Internal Medicine, 1998, vol. 244, pp. 361-370. |
Trust, R. I. et al., "(Aryloxy)[p-(aryloxy)pheny1]- and (Aryloxy)[p-arylthio)phenyl]acetic Acids and Esters as Hypolipidemic Agents," Journal of Medicinal Chemistry, 1979, vol. 22, No. 9, pp. 1068-1074. |
Turner, N. et al., "Insulin Resistance, Impaired Glucose Tolerance and Non-Insulin-Dependent Diabetes, Pathologic Mechanisms and Treatment: Current Status and Therapeutic Possibilities," Prog Drug Res., 1998, pp. 33-94. |
Varma, R.S. et al., "Synthesis of Substituted 2-Phenylbenzothiazoles & 5(6)-Nitro-1, 3-disubsituted-benzimidazoline-2-thiones as CNS Active Agents," Indian Journal of Chemistry, May 1998, vol. 27B, No. 5, pp. 438-442. |
Vedell, E.S., et al., "Differential Effects of Chronic Halofenate Administration on Drug Metabolism in Man," Fed. Proc., Mar.-Apr. 1972, vol. 31, No. 2, p. 538. |
Wilson, J.D., et al. eds. Disorders of Lipid Metabolism, Chapter 23, Textbook of Endocrinology, 9th Edition, 1998, W.B. Sanders Company, Philadelphia: PA. (All References Cited Therein). |
Wright, A.D., et al., "UKPDS 28: A Randomized Trial of Efficacy of Early Addition of Mefformin in Sulfonylurea-Treated Type 2 Diabetes," Diabetes Care, Jan. 1998, vol. 21, No. 1, pp. 87-92. |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100093854A1 (en) * | 2008-04-03 | 2010-04-15 | Diego Broggini | Process for the preparation of (-)-(4-chloro-phenyl)-(3-trifluoromethyl-phenoxy)-acetic acid 2-acetylamino-ethyl ester |
US8541614B2 (en) * | 2008-04-03 | 2013-09-24 | Metabolex, Inc. | Process for the preparation of (−)-(4-chloro-phenyl)-(3-trifluoromethyl-phenoxy)-acetic acid 2-acetylamino-ethyl ester |
US9023856B2 (en) | 2011-11-04 | 2015-05-05 | Cymabay Therapeutics, Inc. | Methods for treating hyperuricemia in patients with gout using halofenate or halogenic acid and a second urate-lowering agent |
US9060987B2 (en) | 2011-11-04 | 2015-06-23 | Cymabay Therapeutics, Inc. | Methods for treating gout flares |
US9433612B2 (en) | 2011-11-04 | 2016-09-06 | Cymabay Therapeutics, Inc. | Methods for treating hyperuricemia in patients with gout using halofenate or halofenic acid and a second urate-lowering agent |
US9439891B2 (en) | 2011-11-04 | 2016-09-13 | Cymabay Therapeutics, Inc. | Methods for treating hyperuricemia in patients with gout using halofenate or halofenic acid and a second urate-lowering agent |
US9801860B2 (en) | 2011-11-04 | 2017-10-31 | Cymabay Therapeutics, Inc. | Methods for treating hyperuricemia in patients with gout using halofenate or halofenic acid and a second urate-lowering agent |
WO2021236395A1 (en) | 2020-05-18 | 2021-11-25 | Cymabay Therapeutics, Inc. | Cb-0406 choline salt |
WO2021236394A1 (en) | 2020-05-18 | 2021-11-25 | Cymabay Therapeutics, Inc. | Cb-0406 tromethamine salt |
Also Published As
Publication number | Publication date |
---|---|
EP1940387A1 (en) | 2008-07-09 |
CA2623350A1 (en) | 2007-04-05 |
SI1940387T1 (sl) | 2013-04-30 |
ES2394973T3 (es) | 2013-02-07 |
EA015673B1 (ru) | 2011-10-31 |
HRP20130001T1 (hr) | 2013-02-28 |
AU2006294950A1 (en) | 2007-04-05 |
KR101309605B1 (ko) | 2013-09-17 |
KR20080050527A (ko) | 2008-06-05 |
EA200800884A1 (ru) | 2008-12-30 |
EP1940387B1 (en) | 2012-11-28 |
HK1119953A1 (en) | 2009-03-20 |
DK1940387T3 (da) | 2013-01-02 |
IL190325A0 (en) | 2009-09-22 |
RS52608B (en) | 2013-04-30 |
JP2009515817A (ja) | 2009-04-16 |
PL1940387T3 (pl) | 2013-02-28 |
PT1940387E (pt) | 2012-12-17 |
US20070072858A1 (en) | 2007-03-29 |
IL190325A (en) | 2013-04-30 |
WO2007038243A1 (en) | 2007-04-05 |
EP1940387A4 (en) | 2010-11-03 |
CA2623350C (en) | 2014-08-19 |
BRPI0616188A2 (pt) | 2011-06-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0674618B1 (en) | Asymmetric process for preparing florfenicol, thiamphenicol, chloramphenicol and oxazoline intermediates | |
US7432394B2 (en) | Resolution of α-(phenoxy) phenylacetic acid derivatives with naphthyl-alkylamines | |
US7714131B2 (en) | Process for the stereoselective preparation of (−)-halofenate and derivatives thereof | |
JP2010229157A (ja) | S−(−)−クロロコハク酸またはその誘導体からr−(−)−カルニチンを調製するための方法 | |
JP2007524614A (ja) | α−(フェノキシ)フェニル酢酸誘導体の分割 | |
HUT68255A (en) | Process for the preparation of beta-phenylisoserine derivatives and use thereof | |
EP1237847A1 (en) | Method for the stereoselective synthesis of cyclic amino acids | |
JPH0461867B2 (US07714131-20100511-C00007.png) | ||
IE67166B1 (en) | New phenylethanolamino- and phenylethanolaminomethyltetralines process for the preparation thereof inermediates in said process and pharmaceutical compositions containing them | |
WO2009139438A1 (ja) | 光学活性カルボン酸の製造方法 | |
KR20060030048A (ko) | α-(페녹시)페닐아세트산 유도체의 분리 | |
MX2008003796A (es) | Proceso para la preparacion estereoselectiva de (-)halofenato y sus derivados | |
WO2003062186A1 (fr) | Sels metalliques d'acide (3s)-3-methoxycarbonyl-4-phenylbutyrique et utilisation de ceux-ci | |
JP2005053781A (ja) | 光学活性な3−(n−メチルアミノ)−1−(2−チエニル)−プロパン−1−オールの製造方法 | |
WO2016147132A1 (en) | A process for the preparation of droxidopa | |
JPH0417938B2 (US07714131-20100511-C00007.png) | ||
JPH03167167A (ja) | 3,4―エポキシ酪酸エステルの製法および中間体 | |
US6864390B2 (en) | Method for the stereoselective synthesis of cyclic amino acids | |
US20060084825A1 (en) | Novel method for the stereoselective synthesis of cyclic amino acids | |
CN101316585A (zh) | 立体选择性制备(-)-卤芬酯的方法及其中间体 | |
JPH10231280A (ja) | 3−アミノ−2−ヒドロキシ−4−フェニルブチロニトリル誘導体の製造方法 | |
JP2004189725A (ja) | 光学活性含フッ素化合物類、及びこれらの製造方法 | |
JPH069549A (ja) | 光学活性アジリジン−2−カルボン酸誘導体及びその製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: METABOLEX, INC.,CALIFORNIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ZHU, YAN;CHENG, PENG;CHEN, XIN;AND OTHERS;REEL/FRAME:018630/0653 Effective date: 20061204 Owner name: METABOLEX, INC.,CALIFORNIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ZHU, YAN;CHENG, PENG;CHEN, XIN;AND OTHERS;REEL/FRAME:018630/0739 Effective date: 20061204 Owner name: METABOLEX, INC., CALIFORNIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ZHU, YAN;CHENG, PENG;CHEN, XIN;AND OTHERS;REEL/FRAME:018630/0653 Effective date: 20061204 Owner name: METABOLEX, INC., CALIFORNIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ZHU, YAN;CHENG, PENG;CHEN, XIN;AND OTHERS;REEL/FRAME:018630/0739 Effective date: 20061204 |
|
AS | Assignment |
Owner name: DIATEX, INC., TEXAS Free format text: LICENSE;ASSIGNOR:METABOLEX, INC.;REEL/FRAME:022835/0388 Effective date: 19980630 Owner name: DIATEX, INC.,TEXAS Free format text: LICENSE;ASSIGNOR:METABOLEX, INC.;REEL/FRAME:022835/0388 Effective date: 19980630 |
|
AS | Assignment |
Owner name: DIATEX, INC., TEXAS Free format text: CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE OF THE DOCUMENT PREVIOUSLY RECORDED ON REEL 022835, FRAME 0388;ASSIGNOR:METABOLEX, INC.;REEL/FRAME:022973/0618 Effective date: 19980630 Owner name: DIATEX, INC.,TEXAS Free format text: CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CON;ASSIGNOR:METABOLEX, INC.;REEL/FRAME:022973/0618 Effective date: 19980630 Owner name: DIATEX, INC., TEXAS Free format text: CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CON;ASSIGNOR:METABOLEX, INC.;REEL/FRAME:022973/0618 Effective date: 19980630 |
|
REMI | Maintenance fee reminder mailed | ||
LAPS | Lapse for failure to pay maintenance fees | ||
REIN | Reinstatement after maintenance fee payment confirmed | ||
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 20140511 |
|
FEPP | Fee payment procedure |
Free format text: PETITION RELATED TO MAINTENANCE FEES GRANTED (ORIGINAL EVENT CODE: PMFG); ENTITY STATUS OF PATENT OWNER: SMALL ENTITY Free format text: PETITION RELATED TO MAINTENANCE FEES FILED (ORIGINAL EVENT CODE: PMFP); ENTITY STATUS OF PATENT OWNER: SMALL ENTITY |
|
PRDP | Patent reinstated due to the acceptance of a late maintenance fee |
Effective date: 20160405 |
|
FPAY | Fee payment |
Year of fee payment: 4 |
|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
SULP | Surcharge for late payment | ||
AS | Assignment |
Owner name: CYMABAY THERAPEUTICS, INC., CALIFORNIA Free format text: CHANGE OF NAME;ASSIGNOR:METABOLEX, INC.;REEL/FRAME:039072/0872 Effective date: 20130330 |
|
AS | Assignment |
Owner name: DIATEX, INC., TEXAS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CYMABAY THERAPEUTICS, INC.;REEL/FRAME:039045/0152 Effective date: 20160629 |
|
AS | Assignment |
Owner name: CYMABAY THERAPEUTICS, INC., CALIFORNIA Free format text: CORRECTIVE ASSIGNMENT TO CORRECT THE CORRECT THE EFFECTIVE DATE OF THE CHANGE OF NAME PREVIOUSLY RECORDED ON REEL 039072 FRAME 0872. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME;ASSIGNOR:METABOLEX, INC.;REEL/FRAME:039431/0651 Effective date: 20130730 |
|
FEPP | Fee payment procedure |
Free format text: PAT HOLDER NO LONGER CLAIMS SMALL ENTITY STATUS, ENTITY STATUS SET TO UNDISCOUNTED (ORIGINAL EVENT CODE: STOL); ENTITY STATUS OF PATENT OWNER: SMALL ENTITY |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 8TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1552) Year of fee payment: 8 |
|
FEPP | Fee payment procedure |
Free format text: ENTITY STATUS SET TO SMALL (ORIGINAL EVENT CODE: SMAL); ENTITY STATUS OF PATENT OWNER: SMALL ENTITY |
|
FEPP | Fee payment procedure |
Free format text: MAINTENANCE FEE REMINDER MAILED (ORIGINAL EVENT CODE: REM.); ENTITY STATUS OF PATENT OWNER: SMALL ENTITY |
|
LAPS | Lapse for failure to pay maintenance fees |
Free format text: PATENT EXPIRED FOR FAILURE TO PAY MAINTENANCE FEES (ORIGINAL EVENT CODE: EXP.); ENTITY STATUS OF PATENT OWNER: SMALL ENTITY |
|
STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |
|
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 20220511 |